1During my first round of law school applications, I didn’t even apply to Yale, Harvard, or Stanford—the mythical “top three” schools. I didn’t think I had a chance at those places. More important, I didn’t think it mattered; all lawyers get good jobs, I assumed. I just needed to get to any law school, and then I’d do fine: a nice salary, a respectable profession, and the American Dream. Then my best friend, Darrell, ran into one of his law school classmates at a popular D.C.

2restaurant. She was bussing tables, simply because that was the only job available to her. On the next round, I gave Yale and Harvard a try.

3I didn’t apply to Stanford—one of the very best schools in the country—and to know why is to understand that the lessons I learned as a kid were sometimes counterproductive. Stanford’s law school application wasn’t the standard combination of college transcript, LSAT score, and essays. It required a personal sign-off from the dean of your college: You had to submit a form, completed by the dean, attesting that you weren’t a loser.

4I didn’t know the dean of my college at Ohio State. It’s a big place. I’m sure she is a lovely person, and the form was clearly little more than a formality. But I just couldn’t ask. I had never met this person, never taken a class with her, and, most of all, didn’t trust her. Whatever virtues she possessed as a person, she was, in the abstract, an outsider. The professors I’d selected to write my letters had gained my trust. I listened to them nearly every day, took their tests, and wrote papers for them. As much as I loved Ohio State and its people for an incredible education and experience, I could not put my fate in the hands of someone I didn’t know. I tried to talk myself into it. I even printed the form and drove it to campus. But when the time came, I crumpled it up and tossed it in the garbage.

5There would be no Stanford Law for J.D.

6I decided that I wanted to go to Yale more than any other school. It had a certain aura—with its small class sizes and unique grading system, Yale billed itself as a low-stress way to jump-start a legal career. But most of its students came from elite private colleges, not large state schools like mine, so I imagined that I had no chance of admission. Nonetheless, I submitted an application online, because that was relatively easy. It was late afternoon on an early spring day, 2010, when my phone rang and the caller ID revealed an unfamiliar 203 area code. I answered, and the voice on the other line told me that he was the director of admissions at Yale Law, and that I’d been admitted to the class of 2013. I was ecstatic and leaped around during the entire three-minute conversation. By the time he said goodbye, I was so out of breath that when I called Aunt Wee to tell her, she thought I’d just gotten into a car accident.

7I was sufficiently committed to going to Yale Law that I was willing to accept the two hundred thousand dollars or so in debt that I knew I’d accrue. Yet the financial aid package Yale offered exceeded my wildest dreams. In my first year, it was nearly a full ride. That wasn’t because of anything I’d done or earned—it was because I was one of the poorest kids in school. Yale offered tens of thousands in need-based aid. It was the first time being so broke paid so well.

8Yale wasn’t just my dream school, it was also the cheapest option on the table.

9The New York Times recently reported that the most expensive schools are paradoxically cheaper for low-income students. Take, for example, a student whose parents earn thirty thousand per year—not a lot of money but not poverty level, either. That student would pay ten thousand for one of the less selective branch campuses of the University of Wisconsin but would pay six thousand at the school’s flagship Madison campus. At Harvard, the student would pay only about thirteen hundred despite tuition of over forty thousand. Of course, kids like me don’t know this. My buddy Nate, a lifelong friend and one of the smartest people I know, wanted to go to the University of Chicago as an undergraduate, but he didn’t apply because he knew he couldn’t afford it. It likely would have cost him considerably less than Ohio State, just as Yale cost considerably less for me than any other school.

10I spent the next few months getting ready to leave. My aunt and uncle’s friend got me that job at a local floor tile distribution warehouse, and I worked there during the summer—driving a forklift, getting tile shipments ready for transport, and sweeping a giant warehouse. By the end of the summer, I’d saved enough not to worry about the move to New Haven.

11The day I moved felt different from every other time I’d moved away from Middletown. I knew when I left for the Marines that I’d return often and that life might bring me back to my hometown for an extended period (indeed it did).

12After four years in the Marines, the move to Columbus for college hadn’t seemed all that significant. I’d become an expert at leaving Middletown for other places, and each time I felt at least a little forlorn. But I knew this time that I was never really coming back. That didn’t bother me. Middletown no longer felt like home.

13On my first day at Yale Law School, there were posters in the hallways announcing an event with Tony Blair, the former British prime minister. I couldn’t believe it: Tony Blair was speaking to a room of a few dozen students?

14If he came to Ohio State, he would have filled an auditorium of a thousand people. “Yeah, he speaks at Yale all the time,” a friend told me. “His son is an undergraduate.” A few days after that, I nearly bumped into a man as I turned a corner to walk into the law school’s main entrance. I said, “Excuse me,” looked up, and realized the man was New York governor George Pataki. These sorts of things happened at least once a week. Yale Law School was like nerd Hollywood, and I never stopped feeling like an awestruck tourist.

15The first semester was structured in a way to make life easy on students.

16While my friends in other law schools were overwhelmed with work and worrying about strict grading curves that effectively placed you in direct competition with your classmates, our dean asked us during orientation to follow our passions, wherever they might lead, and not worry so much about grades.

17Our first four classes were graded on a credit/no credit basis, which made that easy. One of those classes, a constitutional law seminar of sixteen students, became a kind of family for me. We called ourselves the island of misfit toys, as there was no real unifying force to our team—a conservative hillbilly from Appalachia, the supersmart daughter of Indian immigrants, a black Canadian with decades’ worth of street smarts, a neuroscientist from Phoenix, an aspiring civil rights attorney born a few minutes from Yale’s campus, and an extremely progressive lesbian with a fantastic sense of humor, among others—but we became excellent friends.

18That first year at Yale was overwhelming, but in a good way. I’d always been an American history buff, and some of the buildings on campus predated the Revolutionary War. Sometimes I’d walk around campus searching for the placards that identified the ages of buildings. The buildings themselves were breathtakingly beautiful—towering masterpieces of neo-Gothic architecture.

19Inside, intricate stone carvings and wood trim gave the law school an almost medieval feel. You’d even sometimes hear that we went to HLS (Hogwarts Law School). It’s telling that the best way to describe the law school was a reference to a series of fantasy novels.

20Classes were hard, and sometimes required long nights in the library, but they weren’t that hard. A part of me had thought I’d finally be revealed as an intellectual fraud, that the administration would realize they’d made a terrible mistake and send me back to Middletown with their sincerest apologies. Another part of me thought I’d be able to hack it but only with extraordinary dedication; after all, these were the brightest students in the world, and I did not qualify as such. But that didn’t end up being the case. Though there were rare geniuses walking the halls of the law school, most of my fellow students were smart but not intimidatingly so. In classroom discussions and on tests, I largely held my own.

21Not everything came easy. I always fancied myself a decent writer, but when I turned in a sloppy writing assignment to a famously stern professor, he handed it back with some extraordinarily critical commentary. “Not good at all,” he scribbled on one page. On another, he circled a large paragraph and wrote in the margin, “This is a vomit of sentences masquerading as a paragraph. Fix.” I heard through the grapevine that this professor thought Yale should accept only students from places like Harvard, Yale, Stanford, and Princeton: “It’s not our job to do remedial education, and too many of these other kids need it.” That committed me to changing his mind. By the end of the semester, he called my writing “excellent” and admitted that he might have been wrong about state schools. As the first year drew to a close, I felt triumphant—my professors and I got along well, I had earned solid grades, and I had a dream job for the summer —working for the chief counsel for a sitting U.S. senator.

22Yet, for all of the joy and intrigue, Yale planted a seed of doubt in my mind about whether I belonged. This place was so beyond the pale for what I expected of myself. I knew zero Ivy League graduates back home; I was the first person in my nuclear family to go to college and the first person in my extended family to attend a professional school. When I arrived in August 2010, Yale had educated two of the three most recent Supreme Court justices and two of the six most recent presidents, not to mention the sitting secretary of state (Hillary Clinton).

23There was something bizarre about Yale’s social rituals: the cocktail receptions and banquets that served as both professional networking and personal matchmaking events. I lived among newly christened members of what folks back home pejoratively call the “elites,” and by every outward appearance, I was one of them: I am a tall, white, straight male. I have never felt out of place in my entire life. But I did at Yale.

24Part of it has to do with social class. A student survey found that over 95 percent of Yale Law’s students qualified as upper-middle-class or higher, and most of them qualified as outright wealthy. Obviously, I was neither upper- middle-class nor wealthy. Very few people at Yale Law School are like me.

25They may look like me, but for all of the Ivy League’s obsession with diversity, virtually everyone—black, white, Jewish, Muslim, whatever—comes from intact families who never worry about money. Early during my first year, after a late night of drinking with my classmates, we all decided to stop at a New Haven chicken joint. Our large group left an awful mess: dirty plates, chicken bones, ranch dressing and soda splattered on the tables, and so on. I couldn’t imagine leaving it all for some poor guy to clean up, so I stayed behind. Of a dozen classmates, only one person helped me: my buddy Jamil, who also came from a poorer background. Afterward, I told Jamil that we were probably the only people in the school who’d ever had to clean up someone else’s mess. He just nodded his head in silent agreement.

26Even though my experiences were unique, I never felt like a foreigner in Middletown. Most people’s parents had never gone to college. My closest friends had all seen some kind of domestic strife in their life—divorces, remarriages, legal separations, or fathers who spent some time in jail. A few parents worked as lawyers, engineers, or teachers. They were “rich people” to Mamaw, but they were never so rich that I thought of them as fundamentally different. They still lived within walking distance of my house, sent their kids to the same high school, and generally did the same things the rest of us did. It never occurred to me that I didn’t belong, even in the homes of some of my relatively wealthy friends.

27At Yale Law School, I felt like my spaceship had crashed in Oz. People would say with a straight face that a surgeon mother and engineer father were middle-class. In Middletown, $160,000 is an unfathomable salary; at Yale Law School, students expect to earn that amount in the first year after law school.

28Many of them are already worried that it won’t be enough.

29It wasn’t just about the money or my relative lack of it. It was about people’s perceptions. Yale made me feel, for the first time in my life, that others viewed my life with intrigue. Professors and classmates seemed genuinely interested in what seemed to me a superficially boring story: I went to a mediocre public high school, my parents didn’t go to college, and I grew up in Ohio. The same was true of nearly everyone I knew. At Yale, these things were true of no one. Even my service in the Marine Corps was pretty common in Ohio, but at Yale, many of my friends had never spent time with a veteran of America’s newest wars. In other words, I was an anomaly.

30That’s not exactly a bad thing. For much of that first year in law school, I reveled in the fact that I was the only big marine with a Southern twang at my elite law school. But as law school acquaintances became close friends, I became less comfortable with the lies I told about my own past. “My mom is a nurse,” I told them. But of course that wasn’t true anymore. I didn’t really know what my legal father—the one whose name was on my birth certificate—did for a living; he was a total stranger. No one, except my best friends from Middletown whom I asked to read my law school admissions essay, knew about the formative experiences that shaped my life. At Yale, I decided to change that.

31I’m not sure what motivated this change. Part of it is that I stopped being ashamed: My parents’ mistakes were not my fault, so I had no reason to hide them. But I was concerned most of all that no one understood my grandparents’ outsize role in my life. Few of even my closest friends understood how utterly hopeless my life would have been without Mamaw and Papaw. So maybe I just wanted to give credit where credit is due.

32Yet there’s something else. As I realized how different I was from my classmates at Yale, I grew to appreciate how similar I was to the people back home. Most important, I became acutely aware of the inner conflict born of my recent success. On one of my first visits home after classes began, I stopped at a gas station not far from Aunt Wee’s house. The woman at the nearest pump began a conversation, and I noticed that she wore a Yale T-shirt. “Did you go to Yale?” I asked. “No,” she replied, “but my nephew does. Do you?” I wasn’t sure what to say. It was stupid—her nephew went to school there, for Christ’s sake— but I was still uncomfortable admitting that I’d become an Ivy Leaguer. The moment she told me her nephew went to Yale, I had to choose: Was I a Yale Law student, or was I a Middletown kid with hillbilly grandparents? If the former, I could exchange pleasantries and talk about New Haven’s beauty; if the latter, she occupied the other side of an invisible divide and could not to be trusted. At her cocktail parties and fancy dinners, she and her nephew probably even laughed about the unsophisticates of Ohio and how they clung to their guns and religion. I would not join forces with her. My answer was a pathetic attempt at cultural defiance: “No, I don’t go to Yale. But my girlfriend does.” And then I got in my car and drove away.

33This wasn’t one of my prouder moments, but it highlights the inner conflict inspired by rapid upward mobility: I had lied to a stranger to avoid feeling like a traitor. There are lessons to draw here, among them what I’ve noted already: that one consequence of isolation is seeing standard metrics of success as not just unattainable but as the property of people not like us. Mamaw always fought that attitude in me, and for the most part, she was successful.

34Another lesson is that it’s not just our own communities that reinforce the outsider attitude, it’s the places and people that upward mobility connects us with—like my professor who suggested that Yale Law School shouldn’t accept applicants from non-prestigious state schools. There’s no way to quantify how these attitudes affect the working class. We do know that working-class Americans aren’t just less likely to climb the economic ladder, they’re also more likely to fall off even after they’ve reached the top. I imagine that the discomfort they feel at leaving behind much of their identity plays at least a small role in this problem. One way our upper class can promote upward mobility, then, is not only by pushing wise public policies but by opening their hearts and minds to the newcomers who don’t quite belong.

35Though we sing the praises of social mobility, it has its downsides. The term necessarily implies a sort of movement—to a theoretically better life, yes, but also away from something. And you can’t always control the parts of your old life from which you drift. In the past few years, I’ve vacationed in Panama and England. I’ve bought my groceries at Whole Foods. I’ve watched orchestral concerts. I’ve tried to break my addiction to “refined processed sugars” (a term that includes at least one too many words). I’ve worried about racial prejudice in my own family and friends.

36None of these things is bad on its own. In fact, most of them are good— visiting England was a childhood dream; eating less sugar improves health. At the same time, they’ve shown me that social mobility isn’t just about money and economics, it’s about a lifestyle change. The wealthy and the powerful aren’t just wealthy and powerful; they follow a different set of norms and mores. When you go from working-class to professional-class, almost everything about your old life becomes unfashionable at best or unhealthy at worst. At no time was this more obvious than the first (and last) time I took a Yale friend to Cracker Barrel.

37In my youth, it was the height of fine dining—my grandma’s and my favorite restaurant. With Yale friends, it was a greasy public health crisis.

38These aren’t exactly major problems, and if given the option all over again, I’d trade a bit of social discomfort for the life I lead in a heartbeat. But as I realized that in this new world I was the cultural alien, I began to think seriously about questions that had nagged at me since I was a teenager: Why has no one else from my high school made it to the Ivy League? Why are people like me so poorly represented in America’s elite institutions? Why is domestic strife so common in families like mine? Why did I think that places like Yale and Harvard were so unreachable? Why did successful people feel so different?